2,6-Dichlorobenzoic acid → 2-(2,6-dichlorophenylcarbonyloxymethyl) tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide

HRID 743478Notes

Reaction equation

HRID 743478 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].Cl[CH2:13][N:14]1[S:18](=[O:20])(=[O:19])[N:17]2[CH2:21][CH2:22][CH2:23][CH:16]2[C:15]1=[O:24]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([O:6][CH2:13][N:14]1[S:18](=[O:20])(=[O:19])[N:17]2[CH2:21][CH2:22][CH2:23][CH:16]2[C:15]1=[O:24])=[O:5]

Participants

4

Reactant 2

HCID 57582,6-Dichlorobenzoic acidHCID 194244662-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide

Product 1

HCID 544828982-(2,6-dichlorophenylcarbonyloxymethyl) tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of CS2CO3 (0.47 g; 1.44 mmol) in 10 ml of methanol was added 0.55 g (2.88 mmol) of 2,6-dichlorobenzoic acid and the resulting mixture was stirred under nitrogen at room temperature for 3 hours. The above mixture was concentrated in vacuo to remove the excess methanol, the residue suspended in 10 ml of DMF and 2-chloromethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide (0.5 g; 2.6 mmol) was added. The resulting mixture was allowed to react at 90° C. for 3 hours and then cooled. The mixture was poured into ice/water, extracted with ether/ethyl acetate (3:1; 250 ml), and the organic layer was washed with water and brine, and dried. The organic layer was concentrated in vacuo and the residue was purified by silica gel flash chromatography (35% ethyl acetate in hexane) to afford 0.6 g (61%) of 2-(2,6-dichlorophenylcarbonyloxymethyl) tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 and R3 together =-(CH2)3 -) as a solid, m.p. 92°-93.5° C.

Workup

  1. concentrationThe above mixture was concentrated in vacuo
  2. customto remove the excess methanol
  3. customto react at 90° C. for 3 hours
  4. temperaturecooled
  5. extractionextracted with ether/ethyl acetate (3:1; 250 ml)
  6. washthe organic layer was washed with water and brine
  7. customdried
  8. concentrationThe organic layer was concentrated in vacuo
  9. customthe residue was purified by silica gel flash chromatography (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d0e319bbe3334a5685f68ed3a69e034d
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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